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Pickup is fine. I like to wait at the first door or last one because it's easier to spot my driver. When you leave, bridge/tunnel traffic in NYC can be pretty hectic and can take an hour.
PATH if traffic is bad
It's not typically too busy, my Uber's usually take 5-7 minutes to arrive.
Have a few hotels in mind for when you inevitably miss a layover/ have a cancelled flight due to poor airport logistics
D2, I'm already mentally preparing for the delay due to overcrowded airspace. I assume those haven't changed...
Some uber won't take you to NYC.